JP6888796B2 - 有機ナノグリッド、そのナノポリマー及びその製作方法 - Google Patents
有機ナノグリッド、そのナノポリマー及びその製作方法 Download PDFInfo
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- JP6888796B2 JP6888796B2 JP2020528335A JP2020528335A JP6888796B2 JP 6888796 B2 JP6888796 B2 JP 6888796B2 JP 2020528335 A JP2020528335 A JP 2020528335A JP 2020528335 A JP2020528335 A JP 2020528335A JP 6888796 B2 JP6888796 B2 JP 6888796B2
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- nanopolymer
- fluorene
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- 238000004519 manufacturing process Methods 0.000 title claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 40
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 26
- 239000002994 raw material Substances 0.000 claims description 24
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- 229920000642 polymer Polymers 0.000 claims description 14
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- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 10
- -1 fluorene radicals Chemical class 0.000 claims description 9
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
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- HOQAPVYOGBLGOC-UHFFFAOYSA-N 1-ethyl-9h-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2CC HOQAPVYOGBLGOC-UHFFFAOYSA-N 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
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- ZJQCOVBALALRCC-UHFFFAOYSA-N 9-phenyl-9h-fluorene Chemical class C1=CC=CC=C1C1C2=CC=CC=C2C2=CC=CC=C21 ZJQCOVBALALRCC-UHFFFAOYSA-N 0.000 claims description 2
- STGMORHGPQLXMT-UHFFFAOYSA-N 9h-indeno[2,1-c]pyridazine Chemical compound C1=NN=C2CC3=CC=CC=C3C2=C1 STGMORHGPQLXMT-UHFFFAOYSA-N 0.000 claims 1
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- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 6
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 0 CCc1cc(-c2c(*3)cccc2)c3cc1 Chemical compound CCc1cc(-c2c(*3)cccc2)c3cc1 0.000 description 4
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- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
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- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
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- 230000005408 paramagnetism Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical group N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 1
- UGXCHAULTYBNPF-UHFFFAOYSA-N 3,7-dibromoindeno[1,2-c]pyridin-4-one Chemical compound BrC=1C(C2=CC3=CC(=CC=C3C2=CN=1)Br)=O UGXCHAULTYBNPF-UHFFFAOYSA-N 0.000 description 1
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- 238000005452 bending Methods 0.000 description 1
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- OSVHLUXLWQLPIY-KBAYOESNSA-N butyl 2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl]-2-methylpropanoate Chemical compound C(CCC)OC(C(C)(C)C1=CC(=C2[C@H]3[C@H](C(OC2=C1)(C)C)CC[C@H](C3)CO)O)=O OSVHLUXLWQLPIY-KBAYOESNSA-N 0.000 description 1
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- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
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| CN201711188236.2A CN107973797B (zh) | 2017-11-24 | 2017-11-24 | 一种有机纳米格、其纳米聚合物及其制备方法 |
| CN201711188236.2 | 2017-11-24 | ||
| PCT/CN2018/074317 WO2019100582A1 (zh) | 2017-11-24 | 2018-01-26 | 一种有机纳米格、其纳米聚合物及其制备方法 |
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| JP (1) | JP6888796B2 (zh) |
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| CN109524546B (zh) * | 2018-11-14 | 2020-09-22 | 南京邮电大学 | 一种基于纳米格子分子的有机场效应晶体管存储器及其制备方法 |
| CN109516997B (zh) * | 2018-11-22 | 2021-06-22 | 南京邮电大学 | 类芴基风车状纳米格及其制备方法和应用 |
| CN109438454B (zh) * | 2018-11-28 | 2021-09-10 | 南京邮电大学 | 一种纳米缺角格子及其制备方法与光电应用 |
| CN110078738A (zh) * | 2019-05-16 | 2019-08-02 | 南京邮电大学 | 一种具有热活化延迟荧光性质的a-d-a型纳米缺角格子及其制备方法和应用 |
| CN110305299A (zh) * | 2019-07-04 | 2019-10-08 | 南京邮电大学 | 基于共聚芴醇的交联聚合物及其制备方法和用途 |
| CN111763212A (zh) * | 2020-07-30 | 2020-10-13 | 南京邮电大学 | 一种有机纳米格及其制备方法 |
| CN111825680A (zh) * | 2020-08-05 | 2020-10-27 | 南京邮电大学 | 咔唑1,3位傅克合环的环状化合物及其制备方法 |
| CN113321664A (zh) * | 2021-06-16 | 2021-08-31 | 南京邮电大学 | 菱形螺二格及菱形螺二格的制备方法 |
| CN113461695A (zh) * | 2021-07-13 | 2021-10-01 | 南京邮电大学 | 一种基于微反应器合成手画手格芳烃的方法 |
| CN113461713B (zh) * | 2021-07-14 | 2022-07-22 | 南京邮电大学 | 一种cpdt基梯形格分子及其制备方法和应用 |
| CN115417878B (zh) * | 2022-09-13 | 2024-03-15 | 南京邮电大学 | 蒽衍生物咔唑大环化合物、其制备方法及碘阴离子的检测方法 |
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| JP4336483B2 (ja) * | 2002-09-04 | 2009-09-30 | キヤノン株式会社 | ジアザフルオレン化合物及びそれを用いた有機発光素子 |
| DE112004000832T5 (de) * | 2003-05-12 | 2006-03-23 | Sumitomo Chemical Co. Ltd. | Lichtemittierende Polymerzusammensetzung |
| JP2010100770A (ja) * | 2008-10-27 | 2010-05-06 | Mitsubishi Gas Chemical Co Inc | 熱可塑性樹脂の製造方法、ポリエステル樹脂及びポリカーボネート樹脂、ならびにそれらの用途 |
| KR20130067177A (ko) * | 2011-12-13 | 2013-06-21 | 엘지디스플레이 주식회사 | 화합물 및 이를 이용한 유기전계발광소자 |
| CN105348289B (zh) * | 2015-10-30 | 2018-03-02 | 南京邮电大学 | 纳米格子与纳米聚合物格子材料及其制备和应用方法 |
| CN105622901A (zh) * | 2016-03-16 | 2016-06-01 | 南京邮电大学 | 打断共轭型聚合物半导体材料及其制备方法和应用 |
| CN106518892A (zh) * | 2016-09-20 | 2017-03-22 | 南京邮电大学 | 一种给受体型芴基纳米格子材料、制备方法及其应用 |
| CN106496527A (zh) * | 2016-09-20 | 2017-03-15 | 南京邮电大学 | 一种芴基给受体型纳米聚合物、制备方法及其应用 |
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| CN107973797A (zh) | 2018-05-01 |
| CN107973797B (zh) | 2022-09-30 |
| US20210163482A1 (en) | 2021-06-03 |
| JP2021504364A (ja) | 2021-02-15 |
| WO2019100582A1 (zh) | 2019-05-31 |
| US11312717B2 (en) | 2022-04-26 |
| SG11202004615YA (en) | 2020-06-29 |
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